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We got a call from a CEO who was beyond frustrated. "This is the kind of thing," she told us, "that makes me doubt myself as a leader."

"What's up?" we asked.

"My assistant is 100% focused. She's very professional and friendly, but her judgment is horrible. I just can't trust her to make a good decision."

"Run it down," we said.

"Okay, we had a big client meeting scheduled for yesterday. The client had a slight delay, like thirty minutes. The trouble was that we had another big meeting later the same afternoon, across town. I called the client to see whether they wouldn't be more comfortable moving our meeting to next week, and they said fine. They asked if we could meet at our office. I had to run out and I asked my assistant, Brooke, to schedule a conference room and confirm the new date with our client using email. Two simple things for an executive assistant, right?

When I got back to the office, Brooke told me that she hadn't been able to find a free conference room, so she rescheduled the meeting for the following week - another week out, without asking me first. Then she said "I sent the client flowers, to apologize. Flowers! Why would our client want a bouquet of flowers for a rescheduled meeting? I've talked with Brooke about this kind of thing before. She doesn't connect the dots. It's on me. I hired her, and she's a bright young woman and I'm her manager, so I don't blame her.

I blame myself. But what do I do now? I can't walk through every imaginable business situation with her. I'm looking to teach Brooke some meta-skills that will help her with her business decision-making. Right now, it's very lacking, and sometimes I'm terrified of what Brooke might do."

"So she's trying hard to please," said Molly.

"Oh, she's trying like nobody's business," said Ellen, the CEO.

"She wants to go above and beyond, and instead she kind of goes off in a random direction," I said.

""Like the flowers," said Ellen. Once or twice I've asked Brooke to send someone flowers for a business reason. One of our clients became a grandmother and another time we sent a client flowers for her promotion. Brooke extrapolated from that that it was appropriate to send flowers because we had to reschedule a meeting. Now, if I heard that we didn't have a conference room available on a given day I'd have called me - that is, my boss - and asked what to do, because we could reschedule the meeting, or get a conference room elsewhere in our building as we've done before, or even meet at a restaurant.

There are choices. When I talked with Brooke about the incident, I asked her whether she'd been hesitant to call me, and she said she didn't even think of calling me, because she figured she had it covered."

Training is hard. Mentoring can be time-consuming, but we have to do it, because young people - and perhaps all people - learn by example. They have to try something, see what works and what doesn't, have the ability to ask questions and see how the pop-it beads snap together in the business world. Too often, we teach people just what we think they need to know to do their own job. We teach them a very narrow set of activities and tasks.

Then we're frustrated when they don't foresee the consequences of their actions, as they try to apply their narrow understanding of the job to more and more situations, farther and farther afield.

Ellen is in a tough spot, because Brooke has many tremendous and praiseworthy qualities. The place where Brooke needs help turns out to be one of the most complex attributes a job-seeker has, and that's a stew of intellect, instinct and emotional intelligence that leads to good decision-making. It's rare for a person to pop out of college with all those ingredients! They learn how to make good decisions step by step, the way we all did.

I'm always amazed when a job requisition for an administrator, executive assistant or customer service person mentions nothing about judgment and decision-making. Those are the most important attributes for a person in a kid-gloves role.

We mapped out a training plan for Brooke. It was very hands-on and respectful. Ellen was careful to emphasize that she greatly respected Brooke's abilities. At the same time every culture and leader is different and since Brooke and Ellen were meant to operate as a two-person team they needed to be closely in synch on all kinds of issues. In particular, Ellen coached Brooke, the two of them needed to be in step with respect to correspondence, appointments, communication and other 'human' topics. Once Brooke got the new frame for her job, she was fine after a few months.